Metal salts of polymethylenebisimino acids.



' UNITED STATES PATENT FFTE CARL COUTELLE AND ARNOLD MORE, OF ELLBERFELD, GERMANY, ASSIGNORS 'l of SYNTHETIC PATENTS 00., Inc, or

YORK.

1,150,579. Specification of Letters Patent.

No Drawing.

form heavy metal salts, such as copper or zinc salts which have proved to be Valuable remedies against infectious diseases, especially against tuberculosis.

The polymethylenebisimino acids themselves can be produced by allowing polymethylene-diamins or their homologues to react oncyanids and aldehydes or ketones to form dinitrils which are saponified to give the free acids. The production of these acids however is not claimed in the present application. The following examples are given of how much acids can be prepared' Productz'on of .tcifm-methyZene-bis-imz'no' acetic acid-17 6 parts of tetra-methylenediamin are neutralized with dilute hydrochloric acid and then treated with a solution of 270 parts of cyanid of potassium in 400 parts of water. While cooling 300 parts of 40% formaldehyde are added drop by drop.

On the addition of 500 parts of carbonate of potassium,.the, nitril of the tetra-methylenebis-imino acid is precipitated as a semi-solid mass. The latter is treated with alcohol, evaporated, and on cooling a White crystalline mass. of'the melting point of 57 sepa- NEW YQRK, N. Y., A CORPORATION or New METAL SALTS or roLYMErHYLduEBIsIMmo ACIDS.

Patented Aug. 17, 1915.

Application filed October 16, 1913. Serial No. 795,475.

rates out. 170 parts of this nitril are boiled tor 12 to 15 hours with 350 parts of hydrate of barium and 7,500 parts of water. After removing the baryta by means of an equivalent quantity of sulfuric acid, the solution, free from baryta, is evaporated whereu on by cooling the 'tetra-methylene-bis-im1no- I of carbonate of potassium the nitril is sepa rated as light colored yellow oil. 90 parts of the nitril are boiled for 12 hours With 175 parts of hydrate of barium and 3,750 parts of water. After exactly neutralizing and removing the baryta with sulfuric acid and filtering oil the sulfate of barium, the solution, free from barium, is evaporated and thus the beta-methyl-tetra-methylene-bisimino acetic acid is obtained as a non-crystailizable syrup ofhoney yellow color.

, In order to illustrate the, new process more fully the following example is giveinthe parts being by weight :-Beta-methyltetramethylenebisiminoacetic acid is boiled tm gether with an excess of carbonate of copper in aqueous solution. The copper salt is filtered off and dried. It is a bluish crystalline compound soluble in water, but diflicultly soluble in alcohol, ether, acetone. The new copper salt has most probably the following formula:

(iOO Cu--OO containing about 22 per cent. of copper.

We claim: Y

1. As new products, the metal salts of polymethylene bisimino acids containing at least four and not more than five methylene groups which are generally crystalline products soluble inwater and generally soluble with difliculty in organic solvents and which are valuable therapeutics against infectious diseases, substantially as described.

2. As new products, the heavy metal salts of polymethylenebisimino acids containing at least four and not more than five methyl:

ene groups which are generally crystalline products soluble in water and generally soluble with difiiculty in organic solvents andpolymethylenebisimino acids containing at least four and not more than five methylene groups which are generally crystalline products soluble in water and generally soluble with difficulty in organic solvents and which are valuable therapeutics against infectious diseases, substantially as described.

5. As new products, the metal salts of tetramethylenebisimino acids which are generally crystalline products soluble in water and generally soluble with difficulty in organic solvents and which are valuable therapeutics against infectious diseases, substantially as described.

6.. As new products, the divalent metal salts of tetramethylenebisimino acids which aregenerally crystalline products soluble in water and generally soluble with difliculty in organic solvents and which are valuable therapeutics against infectious diseases, substantially as described.

7. As new products, the copper salts of tetraniethylenebisimino acids which are generally crystalline products soluble in water and generallysoluble with difliculty in organic solvents and which are valuable therapeutics against infectious diseases, substantially as described.

8. The new copper salt of beta-methyltetramethylenediamin having most probably the formula:

NH-CHz-CH-CHz-CHz-NH in H; Hz

which crystallizes in light bluish needles soluble in water with a blue coloration, soluble with diiiiculty in alcohol, acetone, ether,

etc, and being a valuable remedy against in- CARL ooUTELpE. [Ls] ARNOLD MORE. [L.s.]

Witnesses HELEN NUFER, ALBERT NUFER. 

